Organic mercury compound.



'r rice.

MAX ENGELMANN, OF ELBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORM.

FRIEDR. BAYER & CO., OEELBERFEIJ). GERMANY, A CORPORATION OF GER-MANY.

ORGANIS MERCURY COMPOUND.

No Drawing.

Specification of Letters Patent.

Patented Aug. 2a, 1911.

Application died September 7, 1910. Serial No. 580,858.

To all whom it may concern:

Be it known that 3., MAX ENGELMANN,C1OC- tor of philosophy, chemist-, citizen of the German Empire, residing at Elbcrfeld, Germany, have 'invented new and useful Improvements in Organic Mercury Compounds, ofwhich the following is a specification.

My invention relates to the preparation of hitherto unknown easily solublecompounds derivedfrom the ortho-oXy-mercuric compound of salicylic acid anhydrid ,(hydrargyrum salicylicum). in order topreparethese products the ortho onymercuricv sahcyhc acid anhydrid (hydrargyrum salicylicum of the German Pharmacopoeia) is treated with salts of imlno compounds containing groups of an acid character; orthe alkaline salts. of. the OItlIOOXYIHQICUIIC salicylic acid anhydrid are treated with 'imino compounds of the class defined or with their salts; or a mixture of the ortho-oxymercuric salicylic acid with theimino compounds is treated with alkali. The imino compounds may vary widely in their chemical constitution;

the only conditions necessary being that they must contain in addition to an imido radical another group or groups imparting an acid character to the compound. Bodies belonging to this class are for instance, acid imids, such as succinic imid, of the formula:

2 NH Hz-C barbituric acids, such as possessing the following formula:

- parabanic acid, of the formula uracids, or their derivatives such as the methyluracil of the formula:

Nn oo 00 on \Na cZcHS They show a more or less strong acid reaction to litmus and form salts showing alkaline reaction. H

The new compounds thus obtained are whitish crystalline odorless which are very easily soluble in water and insoluble inether. They show aneutral reaction againstlitmus and are'notdecomposed by carbonic acid conducted into their solution. They have proved to be yaluable antisyphilitica characterized by a mild action and as they are non-irritants and not corrosive they are highly valuable forinternal application especially for subcutane-- ous injection. They can be used for the preparation of tablets from which aqueous solutions containing definite amounts of,

mercury can be prepared with the greatest They contain the mercury so firmly combined that on adding a diluted solution of caustic alkali o? a cdld solution of amnionium. sulfid no precipitate is obtained. l solut1on of from O.l0.2 grams may be used for one subcutaneous in ection.

compounds In carrying out my invention I can prowith almost theoretical yield. It can be purified by precipitation of its concentrated aqueous solution with alcohol. It is soluble in water yielding a neutral solution, insoluhis in alcohol, ether, benzene, acetone and chloroform; or: a mixture of 350 parts of the ortho-oXy-mercuric compound of salicylic acid anhydrid-(hydrargyrum salicylicum), 128 parts'of diethylbarbituric acid and 2000 parts of normal NaOH is, while being shaken from time to time, allowed to stand for some hours at a moderate temperature. The solution, is filtered and the filtrate concentrated in mono to a syrupy consistency. On addition of alcohol the new compound having probably the following formula separates in crystals.

I claim:

1. The herein described new mercury compounds obtainable by reacting with alkali and an nnlno compound upon orthooxyniercuric salicylic acid anhydrid, which I new mercury compounds probably contain in the r molecule the characteristic group:

in which Me stands for metal, and are whitish powders easily soluble in water and insoluble'in ether, and containing'tlie mereury so firmly combined that the aqueous solutions do not give any precipitate on the addilionof dilute caustic soda lye or a cold solution of ammonium sullid; and being valuable tlici'apcutics, substantially as described.

2. The herein described new sp ecific mercury compound having probably the following formula:

l team obtainable by reacting with alkali and diethylbai'bituric acid upon orthooxymercuric salicylic acid anliydrid which is aflwhitish crystalline powder, easily soluble in Water yielding a neutral solution,- insoluble in alcohol, ethcr, benzene, facctone and chloroform, and containing the mercury solirinly combined that the aqueous solution does not give any precipitate on the addition of dilute caust c soda lye or a cold solution of ammonium siil fid'; and being a valuable therapeutic compound, substantially as described.

In testimony whereof I have hereunto set 

